Often referred to as the Horse Capital of the World, Lexington, Kentucky, lures in visitors for its horses, yes, but also for the incomparable surrounding landscape and the adventures that await within. The city itself is historic – it was founded in 1775 when it was still a part of the state of Virginia. Lexington was booming and cosmopolitan by 1820, and it impresses to this day.

With gentle hills and the surrounding Bluegrass Region, much of Lexington stands erect on limestone, which births the famous poa pratensis grass, more commonly known as bluegrass, and helps to carve the world-renowned caves of Kentucky below. Travelers in Lexington enjoy the Kentucky River, a thriving landscape cushioning the city, abounding horse farms and enough bourbon for everyone. Since Lexington was named the fourth best city for “Businesses and Careers” by Forbes in 2011 and sixth in “Best Value Cities” in 2011 by Kiplinger, the city is expanding with the adventure community in tow. Before it gets too big, visit Lexington with a certainty that you’ll experience the charming downtown area and the unscathed natural beauty that made the city grand.

Hotels

Gratz Park Inn: Centrally located and more charming than your run-of-the-mill corporate chain, Gratz Park Inn gives you easy access to vibrant Lexington and just a short drive from the countryside. In true bed-and-breakfast style, the rooms and suites are all decorated tastefully but differently, yielding a unique experience for each guest. One of the packages at Gratz Park Inn includes a picnic in the park, which you can follow up with a bike ride through the trails of Lexington. From $179.gratzparkinn.com 120 West 2nd Street

Essence of The Bluegrass: This elegant bed-and-breakfast hides within a large brick house in the country outside of Lexington’s center. A double-grand staircase hovers over a grand player piano – the whole place is grand. Just minutes away are some of the best bourbon distilleries and the Kentucky Horse Park, where you can spend the day riding. From $149.essenceofthebluegrass.com343 Mt Horeb Pike

Three Tress Campground: If you’re looking for an accommodations adventure and would rather sleep beneath the stars than a ceiling, check out the Three Trees Campground. Just 16 miles southeast of Lexington, this campground is just across the road from Fort Boonesborough State Park. Three Trees offers canoeing and kayaking, primitive sites, water and showers. The campground is beautifully situated along the Kentucky River. From $28.threetreeskayak.com 300 Athens Boonsboro Road

Eat and Drink

Sahara Mediterranean Cuisine: For a Mediterranean food adventure, check out the lauded Sahara Mediterranean Cuisine, where well-executed staples are served at an affordable price. Grab stuffed grape leaves, falafel or Tabooli to start and finish off with lamb, beef or chicken sandwiches ($5) or dinner plates ($11). Whatever you get from Sahara will be good, but be sure you can get it when you want by checking the restaurant’s hours before you go (they’re closed on Sundays and open 11 a.m. – 7 p.m. all other days while hours in December vary). Stop in on your way south out of town toward the deepest lake in Kentucky, Herrington Lake.sahara-lex.com 3061 Fieldstone Way, Suite #1200

Bourbon n’ Toulouse: You can’t visit Lexington without exploring the area’s bourbon culture. Make a plan to have a meal at Bourbon n’ Toulouse and indulge in some great Creole/Cajon food while you’re sipping your whiskey. Jambalaya, gumbo, crawfish and other southern favorites help complete a menu here that also offers gluten-free and vegetarian options. Since the restaurant is located near downtown, dine before you dash off beyond the city center for fun.bntlexington.com 829 East Euclid Avenue

Adventure Activities

Red River Gorge: Just about an hour outside of Lexington is the Daniel Boone National Forest, which features infinite opportunities for adventure. Red River Gorge, which lies within the park, is a canyon system known for its phenomenal climbs. The area offers sandstone cliffs, natural bridges, rock shelters and waterfalls, ranging in difficulties from the casual to the professional. Zip-lining and hiking are also available within the RRG. Meanwhile, the forest offers hiking, camping, boating and various water activities.redrivergorge.com

Herrington Lake: Whether you’re looking for a place to fish, wakeboard, waterski, tube or boat, Herrington Lake is a perfect day trip. Herrington Lake is the deepest lake in the state of Kentucky, and it’s also just 25 miles outside of Lexington. If you like to golf, try the Peninsula Golf Resort or if you just want to play in and near the water, there are several marinas near the Peninsula Golf Resort for entry. kentuckytourism.com/lakes_rivers/herrington-lake/12/

McConnell Springs Park: Home of the county’s only known sinking springs, McConnell Springs Park is a 26-acre lush and well-preserved natural area within Lexington. Spend the day exploring the trails that run through the park or participating in one of the many educational and community-centric events that take place at McConnell. mcconnellsprings.org 416 Rebmann Lane

Get Around

Fly into the Blue Grass Airport and get into Lexington’s downtown area by renting a car, taking a taxi or hopping on a LexTran bus, which offers express transportation from the airport to downtown. There’s a curbside designated pickup waiting area for the bus right outside of the Blue Grass Airport – follow the signs. You can also utilize the LexTran buses while navigating your way around town, and Google transit integrates well with the network. A $3 day pass will give you unlimited rides for the day. You can also rent a bike from Scheller’s Fitness & Cycles downtown for as low as $29 per day.

Adventure Tip

There are great biking trails running through Lexington and the county, but Legacy Trail is one of the most notable. The 12-mile trail runs from downtown to the Kentucky Horse Park. Other than crossing the busy Newtown Pike, you don’t have to worry about traffic while on this trail, but make sure you take note of this intersection before you begin your journey.

We’ve all been there. Maybe we’ve been one. The person on a guided tour or trip who’s a complete, utter, pain in the ass.

Perhaps it’s unintentional. Maybe it’s due to deep-seated issues that would cause empathy in another situation. Or just possibly, it’s because the person in question gets off on being a jerk. Does it matter? Whether they provide unwitting entertainment or seething aggravation, that person manages to disrupt others’ enjoyment of the experience. The person who really suffers, however, is the guide.

I’ve had good guides, bad guides, guides who should be nominated for sainthood, but regardless of their skill, they have a difficult job. It’s not easy to wrangle any combination of clueless, headstrong, enthusiastic and grumpy tourists, and get them to points A, B and C on schedule – ideally with an unfailingly polite attitude and unwavering smile on your face. It’s a gift, being a guide possessed of technical, personal and mental skills.

Even those who love to travel solo occasionally require the services of a guide. Thirteen years as a travel journalist has given me a lot of material (in part because my favorite thing to ask guides for are bad client stories).

As a holiday gift, I’m providing a list on how to annoy your guide. Follow it, and I promise you’ll always be remembered – just not fondly.

Wear inappropriate clothing/shoes
I had an absolutely priceless two days in the Atacama Desert last year with two middle-aged Chilean couples. Read: they were such drunken louts, it was painful for the rest of us to keep our mouths shut. My favorite experience with them was on a late-afternoon hike of the stunning Kari Gorge.

The key word here is “hike.” To which one of them, a spoiled Santiaguino physician’s wife, wore staggeringly high boots with a narrow wedge heel. She was also completely shit-faced, so when she wasn’t face-planting on the rocky floor of the gorge, she was screaming at her worthless husband to help her climb up the craggier parts of the trail. The rest of our small group finally broke down and pitied her as we summited a steep, mile-long sand dune. She was openly weeping at that point, clutching her chest in panic (a chain-smoker, she thought she was having a heart attack; ironically, her cardiologist husband was the least concerned of all of us).

Because we had to spend so much time waiting for her, we nearly missed the highlight of the excursion, which was watching the sunset from atop a cliff. By not bothering to check what kind of outing she was taking, she kept the rest of us at her mercy, tested our guide’s patience, and subjected us to her marital issues. Um, awkward.Overstate your abilities
Along the same lines, this woman wasn’t fit enough to master a climb up a flight of stairs. It’s not just inconsiderate to fail to accurately access your physical abilities; it can be deadly. At best, it will ensure you and your guide (who will have no choice but to coddle and devote extra time to you) have a miserable time; at worst, you may well end up having that coronary in a sand dune. Don’t be that person.

Bring your bad attitude with you
True story from a sea-kayaking/orca-watching trip I took last summer. We were on the northern tip of San Juan Island, just miles off of Vancouver Island (i.e. Canada). Our guide pointed out this interesting fact to us, which elicited the following response from the one unfriendly person in our group. She was a taciturn woman in her 30s, a self-professed “bird-lady” who owned 12 parrots.

Annoying Client: I made a promise to myself to never leave this country for any reason, whatsoever.

Hapless Guide: That’s an interesting promise. Why?

AC: Because I believe in America. I don’t ever want to support another country’s economy. Why should I? I even go out of my way to buy products made here.

HG: Aah….hmmmm. Okaaay.

I’m not sure what I love most about this incident: that this woman knowingly took a trip to the Canadian border, or that she supports exotic bird smuggling from foreign countries.

Be late/unprepared
A great way to piss off your guide, and everyone else in your group. Also helpful in ensuring you won’t get your money’s worth from your trip or tour, since the schedule will be compromised. This one’s a winner!

Whine
Because nothing is better for group morale than someone who complains about everything.

Engage in excessive PDA with your significant other
It may start off as amusing for your guide and fellow travelers. Trust me, by trip’s end, they’ll be ready to kill you. Get a room.Don’t pitch in
Hey, Princess. I know you paid a chunk of change for this (fill in the blank: raft trip/backpacking trip/guest ranch stay). So did everyone else. But your guide and support staff are working their fingers to the bone for very little pay because they love what they do. You know what else they love? Guests or clients who make even the smallest effort to help them out. Ask where you should stash your gear, collect firewood, help chop vegetables or cook dinner (right). Not only will you gain their respect and gratitude, you may even enjoy yourself.

Be high-maintenance
It’s not all about you. You have a pretty good idea of what you’re getting into when you sign up.

Forget to mention your “dietary restrictions”/preferences
Travel companies are savvy enough these days to always include a section for this on their registration forms; I’m not talking about legitimate food allergies or intolerances. But please be honest, not ridiculous, and if you don’t like what’s being served, be polite about it – especially if you’re in a foreign country.

Refuse to interact with your group
I can be a bit of an introvert, so I get how hard it can be to socialize with a group when you’re just not feeling it. But guides tend to stress about the lone client, and feel pressure to ensure they’re having a good time. If you really don’t feel like socializing, assure your guide that you’re just shy, but having a great time. Otherwise, I really recommend faking it till you make it. Once I come out of my shell, I’m usually grateful, because I end up meeting fantastic people who make my experience that much more interesting.